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Standing in a bar one night in Santorini, Ken Kessler struck up a conversation with a chatty blonde. A keen traveler, the retired salesman from Evanston, Illinois, was astonished to find out that she lived in Nairobi, Kenya. “I’m in the safari business,” she told him. Months later, that late-night encounter led to an unforgettable trip to Africa for Kessler, his wife and daughter—their entire experience coordinated by that same blonde, Lisa Rolls, a professional guide and co-owner of Virgin Bush Safaris.

“It was a chance encounter, so I took a chance,” explains Kessler, who still marvels at Rolls’s impact on his trip. At one point she floated the idea of seeing the house where Out of Africa was filmed. “Bingo bango, we get in the car and her buddy is an artist who owns the house,” says Kessler. “So we go over and see it.”

More soberly, after a connecting flight to Arusha in Tanzania, Kessler queried a sign at the airport proclaiming “The Switzerland of Africa.” It sparked lengthy conversation about the trials nearby in the wake of Rwandan genocide. Ninety minutes later, thanks to Rolls’s connections and initiative, Kessler and his clan found themselves sitting in the viewing gallery at the U.N. courthouse.

“You can plan all you want, but you can’t get the same experience as with a well-connected guide,” he says. “They know everybody.”

With the proliferation of guides out there, it is more important than ever to sift out the best—those who are able to plan ahead, anticipate travelers’ interests and react resourcefully to spontaneous ideas. Before booking a tour, Kessler suggests asking for two or three past traveler references, and querying passengers extensively about their experiences.

Don’t be put off by the tricky issue of tipping, adds travel consultant Ellison Poe. “It’s a taboo—no one wants to tip somebody more than they’re paid in a month,” she says. “So appropriate tipping is a huge issue.” The safest default is to calculate 10 to 15 percent of the cost, discreetly paid in cash at tour’s end.

The onus of a great experience doesn’t lie with an escort alone, though. To maximize the time, a savvy traveler should research enough to give clear direction. Sharper parameters at the outset allow for a more satisfying outcome, which is one of the reasons many of the best upscale guides have clearly established niches. Take Rome-based Iris Carulli, who focuses entirely on art and has earned a place in the black books of museum directors, or Antwerp’s Tanguy Ottomer, a fashionista fixer with intimate connections across the city’s edgy style scene.

Here is our elite list of the world’s greatest guides, with expertise that spans from Venice to the veldt of Africa.